The Paradox Of The Serial Entrepreneur - Social Media Explorer
The Paradox Of The Serial Entrepreneur
The Paradox Of The Serial Entrepreneur

I’m always amused when someone proudly describes what they are or do by using the term, “serial entrepreneur.” The more technology companies I encounter, the more founders and C-level folks waive that banner as if it’s some sort of badge of honor.

I suppose if you’ve created and sold a number of companies for lots of money, being a serial entrepreneur is a good thing. But most people who use the term (at least to me) have only started several companies. They’ve never sold them.

What they’re really saying by “serial entrepreneur” is one or more of the following:

  • None of my ideas have worked
  • I can’t raise money
  • I have no attention span
  • My passion is about getting lucky and making a wad of money

A friend of mine calls himself a serial entrepreneur. He helped build one company as a young man and made a meager profit as a vested employee. He then started his own company, spent 10 years building it and sold it for low seven-figures. He’s now on his second company that he started with only himself and his former business partner as an investor. They’ve been at it six years now. He’s in his 50s.

When someone that age and with that history tells me he’s a serial entrepreneur, he’s saying:

  • I know how to build a company
  • I know how to sell a company
  • I’m focused on my business
  • My passion is about building something of value

It’s a different spin and it’s not subtle.

If you’re calling yourself a serial entrepreneur and you have as many companies or ideas as you have zits, you’re not impressing anyone. In fact, you may be hurting your chances of making headway toward becoming a real one.

Food for thought. Yours are welcome in the comments.

About the Author

Jason Falls
Jason Falls is the founder of Social Media Explorer and one of the most notable and outspoken voices in the social media marketing industry. He is a noted marketing keynote speaker, author of two books and unapologetic bourbon aficionado. He can also be found at
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  • Abercrom

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  • ndawkins

    Here is a different view:  RH Macy founded 7 businesses before his hit with Macy’s.  Henry Ford’s early businesses left him broke 5 times.  Even Bill Gates fell flat on his face the first time around the entrepreneurial block.  Entrepreneurs who never fail are rare.  In fact, sit in on any Vistage meeting (formerly Tec, this is the largest CEO membership organization in the world) and you’ll find a group of people who VALUE failure.  They want people in their group who have succeeded AND who have failed, because individuals can’t learn, society can’t learn, even business schools can’t learn, without failure.  Part of being an entrepreneur is having a pioneer spirit and being unfazed by the possibility — or the ugly reality — of failure.

    Also, re the definition of success:  Selling a company isn’t necessarily successful.  Talk to some folks who have sold for stock.  Or to one of the thousands of little companies purchased each year who watch their baby get put up on a shelf and forgotten or run into the ground.  Is that a success?   And why is sticking to a single vision/company all of your life a criteria for respect as an entrepreneur?  My grandfather had 11 different businesses throughout his lifetime; some
    were complete failures, some just weren’t successful enough to warrant
    continuing.  There is no shame in that.  He fed his family, he employed many people, he created business for his community. That’s not success?

    Finally, an “entrepreneur” is not just someone who founds or owns the majority stake of a company.  Every start-up employee who lays down his/her blood, sweat and tears to build something on the hope of maybe one day realizing a financial return beyond salary is an entrepreneur.  I’ve been one of those people in the past and today I thank my lucky stars that I have those folks around me.  They too, are entrepreneurs, and they are unfazed by failure.

  • I’ve always thought an entrepreneur is someone who sees a problem and
    comes up with a product or service to solve that problem over the long

  • I love your contrasted definitions.  I think many who call themselves serial entrepreneurs are wishfully so more than factually so ;)

  • clarestweets

    Excellent advice with several great takeaways. 1) Stay committed. Entrepreneurship is hard and staying with it even harder.2) Learn from your past –success and failures. 3) Most important, build something of value! Thanks Jason.   

  • The only other famous “serial” anything is a killer. 

    I actually am one of those, but I also sold my first two companies before starting this one.

  • Hah! That’s exactly what I think when I hear “I’m a serial entrepreneur”. You nailed it. And I just had a conversation with someone who proudly proclaimed themselves a serial entrepreneur. I pretty much turned off the listen mode and went into “hmmm, wonder when I can get back to the office and do ….” which means I no longer take them seriously. 

  • Jason, it seems like many these days use the term ‘entrepreneur’ to mean come up with an abstract idea, attract venture capital, grow as big as possible, then sellout to other company or take it public in order to retire on a beach somewhere. 

    I’ve always thought an entrepreneur is someone who sees a problem and comes up with a product or service to solve that problem over the long haul, not such a short-sighted definition that seems to currently be in vogue. 

  • Perhaps you are misinterpreting them…maybe they mean that they are a CEREAL Entrepreneur and spend their weekends making necklaces and earrings out of Froot Loops and Captain Crunch!

  • Nice post!  Very straightforward.  Have to admit I have been guilty of being the 1st type of “serial entrepreneur” although I have not bragged about it…the goal is to become the 2nd type of “serial entrepreneur.  Thanks for posting this Jason.